5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → 4-(5-chloro-[1H]-indol-3-yl)-piperidine

HRID 324364ノート

反応式

HRID 324364 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1>C(O)(=O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

参加物

4

反応物 1

HCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

生成物 1

HCID 128313754-(5-chloro-[1H]-indol-3-yl)-piperidine収率 72.4%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 176Acetic Acid溶媒

実験手順

Crude 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 8a (26 g) was dissolved in glacial acetic acid (330 ml) and PtO2 (0.7 g) was added. The mixture was hydrogenated in a Parr apparatus at 3 atm. for 5 hours. The catalyst was filtered off and excess acetic acid evaporated in vacuo. Water was added and pH was adjusted to >9 by addition of diluted aqueous NH4OH. Extraction with ethyl acetate (2×200 ml) and work-up of the combined organic phases yielded 19 g of crude title compound as a visceous oil.

後処理

  1. filtrationThe catalyst was filtered off
  2. customexcess acetic acid evaporated in vacuo
  3. additionWater was added
  4. additionpH was adjusted to >9 by addition of diluted aqueous NH4OH
  5. extractionExtraction with ethyl acetate (2×200 ml)

出典と根拠

ORDレコード
ord-ff69e88d733d461b81af5a9902e85653
出典データセット
uspto-grants-2001_04
特許番号
US06218394B1

反応ノート

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